Signors to l g



\ Patented Apr. 9, 1929.

UNITED STATES PATENT OFFICE.

KARL MARX, KARL BRODERSEN, AND KARL BITTNER, OF DESSAU, GERMANY, AS-SIGNORS TO I. G FARBENINIDUSTRIE AKTIENGESELLSCHAFT, OF FRANKFORT-ON-THE-MAIN, GERMANY.

MANUFACTURE OF AGENTS FOR R Drawing.

The present invention relates/to ne agents for emulsifying, purifying,wetting and the like uses and to a process of preparing the same.

Our new products are obtainable by treating with a sulphonating agent amixture of a brown coal tar oil and a compound containing an aromaticnucleus. The 1, term a brown coal tar oil as used in die specificationand'the claims is intended to include, for instance, solar oil, yellowoil, gas oil, paraflin oil, and mixtures of hydrocarbons obtainable frombrown coal tar. The term a compound containing an aromatic nucleuscomprises such compounds as benzene,

xylene, solvent naphtha, naphthalene, tetrahydronaphthalene,chlorobenzene, chloronaphthalene and'anthracene, as well as mix tures ofany of these. I

Preferably the process is carried out by treating a mixture of aboutequal parts of brown coal tar oil and a compound containing an aromaticnucleus with chlorosul-- phonic acid at low temperatures, i. 0.,temperatures of, for instance, about 5 C. to about (3..

7 Our products form as sodium salts white to yellowish-brown powdersbeing easily soluble in water and dilficultly soluble in organicsolvents.

Thenew agents show in general an activity which considerably exceedsthat of a mixture of their sulphonated constituents used alone. Forexample, whereas on the one hand a sulphonic acid made-from Solar oil bymeans of chloro-sulphonic acid shows in Traubes stalagmometer (water No."a drop number of 76 for a solution of the sodium' salt of 0.5 per centstrength, and on the other hand a sulphonic acid made from solventnaphtha by means of chlorosulphonic acid shows under like conditions adrop number of only 61, an agent obtained as described in the subjoinedExample 1 shows a drop number of 83.

Instead of treating with a sulphonating agent a mixture of a brown coaltar oil and a compound containing an aromatic nucleus, the process maybe carried out in such a way that at first one constituent may betreated with a suiphonating agent and then the second constituent addedand, if necessary,

the mixture further sulphonated.

EMULSIFYING, PURIFYING, WET'I ING, OR THE LIKE BY SULPHQNATION.

Application filed May 18, 1927, Serial No. 192,478, and in Germany May19, 1826.

. The following examples illustrate the invention, the parts being byweight Eat-ample 1.To 300 parts of solvent naphtha mixed with 300 partsof Solar oil (from brown coal-tar) there are added gradually 600 partsof chlorosulphonic acid at 30 C. while stirring. The mixture is stirredfor some timeand after unchanged oil has been separated in the usualmanner the sulphonic acid is isolated as sodium salt.- It forms ayellowish-brown powder which is easily Soluble in water and dil'licultlysoluble in organic solvents.

Example 2.300 parts of yellow oil are mixed with 300 parts oftetrahydronaphthw lcne and in the course of 2 hours 600 parts ofchlorosulphonic acid are added at a low temperature.' Stirring iscontinued for 2 hours and the product is worked up as described inExample 1. It has the properties hereinbefore indicated.

Ewm'npie 5.To 30 parts of Solar oil dissolved,in 150 partsofchlorobenzene, parts of chlorosulphonic acid are added at -5 C. during2 hours and the mixture is stirred for 2 hours. The product is worked upas described in Example 1. It has properties similar to those of theproducts of the foregoing examples. V

Like products are obtained if another sulphonatin agent, such assulphuric acid of 66 B. o fuming sulphuric acid is used instead of clorosulphonlc acid.

The products have excellent wetting and emulsifying properties and areuseful for various purposes, for-instance, dyeing and washing oftxtilesand destroying animal 3. The process of preparing agents for .7

emulsifying, purifying, wetting and the like emulsifying, purifying,wetting an the like uses which comprises treating with a sul phonatingagent a mixture of Solar oil and solvent naphtha.

5. The process of preparing agents for emulsifying, purifying, wettingand the like uses which comprises treating withichlor'osulphonic acid ata temperature of from about 5 C. .to about +30 C. a brown coal tar oiland a compound containing an aro- 5 matic nucleus.

6. The process of preparingagents for emulsifying, purifying, wettingand the like uses which comprises treating with chlorosulphonic acid ata temperature of from about -5 C. to about,'+30 C. a, mixture of a browncoal tar oil and solvent naphtha.

7. The process of preparing agents for uemulsifying, purifying, wettingand the like uses which comprises treating with about 600 partsofchlorosulphonic acid at a temperature not in excess ofabout C. amixture of about 30 parts of Solar oil and about 300 parts of solventnaphtha.

8. As new agents for emulsifying, purifying, wetting and the like usesthe compoum s being obtainable by treating with a sulphonating agent amixture of a brown tar coal tar oil and a compound containing anaromatic nucleus forming as sodium salts white to yellowish-brownpowders being easily soluble in water and difiicultly soluble inorganicsolvents, their aqueous solutions having a high emulsifying, purifyingand wettlng property.

9. As a new agent for emulsifying, purifying, wetting and the like usesthe com pound being obtainable by treating with about 600 parts ofchlorosulphonic acld at a temperature not in excess of about +30 C. amixture of about 300 parts of solvent naphtha and 300 parts of Solaroil, said compound formin a yellowish-brown powder being easily so ublein water and difiicultly soluble in organic solvents, its aqueoussolution having a high emulsifying, purifying and wetting property.

In testimony whereof We afiix our signatures. KARL MARX.

KARL BRQDERSEN. KARL BITTNER.

